协同对映选择性氨基酸和路易斯酸催化实现的不对称反应

IF 7.1 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Topics in Current Chemistry Pub Date : 2019-11-25 DOI:10.1007/s41061-019-0261-4
Pier Giorgio Cozzi, Andrea Gualandi, Simone Potenti, Francesco Calogero, Giacomo Rodeghiero
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引用次数: 53

摘要

有机催化是催化的一个分支,以小有机分子为催化剂,在过去十年中,它在不对称催化领域中变得至关重要,以至于现在可以与金属催化和生物催化相媲美。基于在有机催化剂和有机底物之间形成共价或非共价中间体,有机催化被合理化和分类为许多所谓的激活模式。在所有的有机催化活化方式中,无论是在学术上还是在工业上,烯胺和胺催化都被广泛用于实际制备有价值的产品和中间体。在这两种情况下,手性胺被用作催化剂。与亲电试剂的反应一般采用烯胺活化方式,而亲核试剂则需要最小活化方式。通常,在这两种模式中,反应都是通过组织良好的过渡态发生的。由于胺类和胺类离子具有足够的亲核性和亲电性,大量的络合物可以分别与它们发生反应。然而,尽管取得了成功,有机催化仍然受到范围和应用范围的限制。多催化是一种可能的解决方案,因为两种不同的催化剂可以协同激活底物,同时激活两种不同的反应伙伴。特别是,在这篇综述中,我们将总结Lewis酸催化和有机催化活化模式协同作用而互不干扰的报道过程。我们将把注意力集中在不能通过有机催化或路易斯酸催化独立获得良好结果的过程的描述上。在这些协同双重催化的例子中,已经发展出一些新的有机转化。本文将重点讨论Lewis酸的选择和催化循环等可能的策略。此外,关于有效组合的基本原理的一些重要关键点也将包括在内。本文还将讨论路易斯酸通过形成亲电中间体对有机底物的π活化及其与胺的反应。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Asymmetric Reactions Enabled by Cooperative Enantioselective Amino- and Lewis Acid Catalysis

Organocatalysis—the branch of catalysis featuring small organic molecules as the catalysts—has, in the last decade, become of central importance in the field of asymmetric catalysis, so much that it is now comparable to metal catalysis and biocatalysis. Organocatalysis is rationalized and classified by a number of so-called activation modes, based on the formation of a covalent or not-covalent intermediate between the organocatalyst and the organic substrate. Among all the organocatalytic activation modes, enamine and iminium catalysis are widely used for the practical preparation of valuable products and intermediates, both in academic and industrial contexts. In both cases, chiral amines are employed as catalysts. Enamine activation mode is generally employed in the reaction with electrophiles, while nucleophiles require the iminium activation mode. Commonly, in both modes, the reaction occurs through well-organized transitions states. A large variety of partners can react with enamines and iminium ions, due to their sufficient nucleophilicity and electrophilicity, respectively. However, despite the success, organocatalysis still suffers from narrow scopes and applications. Multicatalysis is a possible solution for these drawbacks because the two different catalysts can synergistically activate the substrates, with a simultaneous activation of the two different reaction partners. In particular, in this review we will summarize the reported processes featuring Lewis acid catalysis and organocatalytic activation modes synergically acting and not interfering with each other. We will focus our attention on the description of processes in which good results cannot be achieved independently by organocatalysis or Lewis acid catalysis. In these examples of cooperative dual catalysis, a number of new organic transformations have been developed. The review will focus on the possible strategies, the choice of the Lewis acid and the catalytic cycles involved in the effective reported combination. Additionally, some important key points regarding the rationale for the effective combinations will be also included. π-Activation of organic substrates by Lewis acids, via formation of electrophilic intermediates, and their reaction with enamines will be also discussed in this review.

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来源期刊
Topics in Current Chemistry
Topics in Current Chemistry Chemistry-General Chemistry
CiteScore
13.70
自引率
1.20%
发文量
48
期刊介绍: Topics in Current Chemistry is a journal that presents critical reviews of present and future trends in modern chemical research. It covers all areas of chemical science, including interactions with related disciplines like biology, medicine, physics, and materials science. The articles in this journal are organized into thematic collections, offering a comprehensive perspective on emerging research to non-specialist readers in academia or industry. Each review article focuses on one aspect of the topic and provides a critical survey, placing it in the context of the collection. Selected examples highlight significant developments from the past 5 to 10 years. Instead of providing an exhaustive summary or extensive data, the articles concentrate on methodological thinking. This approach allows non-specialist readers to understand the information fully and presents the potential prospects for future developments.
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